Anthraquinone vat dyestuff containing a reactive triazing nucleus



3,022,304 ANTHRAQUTNGNE VAT DYESTUFF CONTAINING A REACTWE TRIAZTNE NUCLEUS Max Staeubie, Basel, and Kurt Weber, Eottmingen,

Switzerland, assignors to Ciba Limited, Basel, Switzerland No Drawing. Filed May 25, 1959, Ser. No. 815,266 Claims priority, application Switzerland May 30, 1958 1 Claim. (Cl. 260-249) This invention is directed to a new and valuable anthraquinone vat dyestufi of the formula NH 0 H H 31 V n \N cm-ornoso n m t A Na N CHz-CHa-OSOgH The following examples illustrate the invention, the parts and percentages being by weight:

Example 1 23 parts of :5'-dia1nino-1:1'-dianthrimide carbazole are heated in 600 parts of nitrobenzene with 37 parts of cyanuric chloride for 20 hours at 160 C. After 4 hours 1 part of pyridine is added to the reaction mixture. The whole is allowed to cool and the product is filtered off, washed successively with nitrobenzene, benzene and chloroform and dried at 100 C. under reduced pressure.

12.1 parts of the condensation product thus obtained, which corresponds to the formula l NH $1 0 1 f Hz-N O (i NEE-C 23-411 are stirred in 100 parts of nitrobenzene for 15 minutes at 90 C. In the course of 5 hours, 4.2 parts of diethanolamine in 50 parts of chloroform are then slowly added dropwise, and the whole is maintained for 17 hours at 90 C., and then allowed to cool. The product is filtered oif, washed successively with benzene, alcohol and water and dried at 100 C. in vacuo.

parts of the resulting condensation product of the formula are dissolved in the course of 10 minutes at 0 to 5 C. in 100 parts of sulfuric acid of 100% strength, and the resulting solution is immediately poured cautiously over 1000 parts of ice. The precipitated product is filtered off, washed with cold water until it is neutral, and dried at to C. under reduced pressure.

The dyestuit of the formula NH O o H l I I H N/ /CH2CH2OSO3H HZN 0 0 6 N Example 2 1 part of the dyestulf obtained as described in Example 1 is pasted with 250 parts of warm Water. The resulting dyestutf suspension is added to a solution, heated at 50 C., of 10 parts by volume of sodium hydroxide solution of 30% strength and 6 parts of sodium hydrosulfite in 1750 parts of water, and the mixtureis vatted for 1 minute. 50 parts of cotton are dyed in the resulting dyebath for 45 minutes at 50 to 60 C. with thev addition of 60 parts of sodium chloride. The dyed material is washed, oxidized, acidified, again thoroughly rinsed, and finally soaped at the boil. A brown-orange dyeing of very good fastness properties is obtained.

What is claimed is:

The dyestuif of the formula 31 N 151 OHz-CHaOSOaH HEN 0 0 NH- o- N oHrom-osmH References Cited in the file of this patent UNITED STATES PATENTS 1,437,783 Steinbuch et a1. Dec. 5, 1922 1,523,308 Steinbuch et a1 J an. 13, 1925 1,888,631 Kunz Nov. 22, 1932 1,897,428 Hentrich et a1 Feb. 14, 1933 2,373,826 Graham Apr. 17, 1945 2,671,785 Hardy et a1 Mar. 9, 1954 2,671,786 Scalera Mar. 9, 1954 2,773,871 Brassel et a1 Dec. 11, 1956 2,889,323 Heslop June 2, 1959 2,951,842 Ebel et a1 Sept. 6, 1960 FOREIGN PATENTS 449,477 Great Britain June 24, 1936 802,935 Great Britain Oct. 15, 1958 91,206 Norway Jan. 18, 1958 

